HCID 22648122, compound → N-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-1-methyl-1H-imidazole-4-sulfonamide

HRID 394197Notes

Reaction equation

HRID 394197 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([NH:18][S:19]([C:22]2[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=2)(=[O:21])=[O:20])[CH:15]=[C:14]2[C:9]=1[CH2:10][N:11](CC1C=CC(OC)=CC=1)[C:12](=[O:36])[N:13]2[C:28]1[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:35]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([NH:18][S:19]([C:22]2[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=2)(=[O:21])=[O:20])[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:36])[N:13]2[C:28]1[C:29]([Cl:35])=[CH:30][CH:31]=[CH:32][C:33]=1[Cl:34]

Participants

3

Reactant 1

HCID 22648122HCID 22648122, compound

Product 1

HCID 22648114N-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-1-methyl-1H-imidazole-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-1-methyl-1H-imidazole-4-sulfonamide (114 mg, 0.17 mmol) in 1.5 mL of trifluoroacetic acid was stirred at rt overnight. The resulting reaction mixture was concentrated under reduced pressure, diluted with CH2Cl2 and washed with saturated aqueous NaHCO3 followed by brine. The organic layer was dried with Na2SO4 and concentrated under reduced pressure. The crude solid was purified by preparatory thin-layer chromatography, eluting with 90:10 CH2Cl2-2M NH3 in methanol to yield N-[5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl]-1-methyl-1H-imidazole-4-sulfonamide. Mass spectrum (ESI) 562 (M+1). 1H NMR (500 MHz, DMSO-d6): δ 3.67 (s, 3H); 3.93 (½ ABq, J=14.9 Hz, 1H); 3.99 (½ ABq, J=14.9 Hz, 1H); 4.02 (s, 1H); 5.95 (d, J=2.1 Hz, 1H); 6.55 (d, J=1.9 Hz, 1H); 7.30 (m, 2H); 7.35 (s, 1H); 7.43 (m, 2H); 7.58 (m, 2H); 7.69 (s, 1H); 7.72 (d, J=8.2 Hz, 2H).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. additiondiluted with CH2Cl2
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialThe organic layer was dried with Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude solid was purified by preparatory thin-layer chromatography
  8. washeluting with 90:10 CH2Cl2-2M NH3 in methanol

Sources & evidence

ORD record
ord-cec985d65bf445e0b1534fd62b37c7b0
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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